Complex compound of pentavalent antimony with aromatic polyhydroxy compounds



The presentinv nti v J S T-AT ES PATENT I orFicE.

1,988,576 V COMPLEX- ]coMPoUNn F PENTAVALENT .inNTrMo Yf WITH. AROMATIC POLYHY- nRoxYoo roUrms Hans Schmidt, Elberfeld-lohwinkel, Germany,

assignor to Winthrop Chemical Company,. Inc.,

po nds; o ptn aii ent ientimqnyl 1 wit ar matic pg hyd xycemmim sa dto a p cessof preev u lesalt e o t e t, u qaa -erq iet e n i-rhv'q yc po dr fln in nt at l t wql mx s pu s in hcpositiontoeachothrand i least t e id ou capabl ,o q rm a w ch soluble salt, thatriafa, rboxylic acid or a sulfonic acid group, and which polyhydroxy compound "i; may} belgotherwi'se substituted. Suitable arocen lde t e s 9 t m ti a i s M PJIWSQ i We nv ntnwre. erexem P te in m qa nd;

the complex compound, formed uepe as' substantiallY ,onj thegr mtiv I q oportionzfof jthegstarting components used; gen any I mj working with about; molecular qu tities,b itis to b'e understood'thatthe compounds obta na le by working. with, ,other proportions, .forf fj,exai ip };f when reacting with about'bil mo antimonyl'compound proportionsu ofg an ular. proportion of the about two molecular polyhy'droxy com poundof the, above the tionedlkind, areiincluded within, the scope of my invention." 1"

":1. The proces'sj -islcarried out byfdissolving togther in ,water thefcompoii'ents an heating the reaction mixture prer ram f on a waterbath". for j somehours. Whehstailli with a water-soluble salt of'an aromatic"ortho dihydroxy-carboxylic- *2? or sulfonic-acid and a water-soluble antimonate,

the complex compound is formed immediately after mixing together the components.

To obtain compounds having a neutral reaction in aqueous solution, it is very often neces- 5 sary for the reaction to be carried out with the addition of an alkali. The term alkali may be conveniently used to designate both fixed and volatile alkalies, for instance, ammonia as well as amines and is used in that sense in the appended 50 claims, Otherwise neutralization may be effected afterwards when the reaction is complete. The complex compounds are separated by evaporating the reaction mixture to dryness or by pouring the reaction mixture. into an organic precipitant,

55 such as acetone or methyl alcohol. They are lates to coml 06m;

lt ii e t-l ewtt lr n e ant mony with; romatic repare b cau tw sted, n q 'el e mono and disulfonirz, acid, pyrocatechin-cary be' varied within N ew" York, ;N.- 17.,acorporation of :New York oi Draw ingl -Application November 1, 1929, -Serial=-No. In Germany November 6,

icolaiinsl (01. 2 0 -11 obtainedinjtheform of faintly colored powders, easily soluble in .water, from which aqueous solution=hydrogen sulfide precipitates antimonyl sulfide, and they are less toxic than the correspond; ing compounds containingantimony in the trivalent form as are described,for example, i in U."S; Patent 1,549,154, dated'cAugust 11,1925 when usedfor-medical purposes. 1

The invention is illustrated by the following examples, without being limitedtheretozx Example 1. -20 grams of potassium pyrocatechin disulfonate are dissolvedrin l00-ccm.fof water and the solution isheated'for a short time with .an excess of. antimonic acid. (preferably in the freshly precipitated state); The mixture is allowed to cool, filtered from undissolved substances, the filtrate is neutralized with dilute caustic potash and precipitated by pouringinto methyl alcohol. A whitishspowder islobtained, readily soluble in water.';. i.' r a r Example 2.- grams of 'diethylaminoethanol antimonate, obtainable, for example, by dissolvin'g. antimonic acid in diethylaminoethanol, filtering and evaporating, are dissolved in 15 com. of water and 14.5 grams of potassium pyrogallol'disulfonate (see Beilstein, 4th edition, vol. XI, page 311, line 3 from the bottom) are likewise dissolved in 30 ccmnof water by heating. The twosolutions are mixed,rneutralized with dilute diethylaminoethanol solution and the solution is evaporated or the antimony complex salt formed is'precipitated by. pouring. into methyl alcohol.

The complex salt dissolves readily in water and the solution remains clear on addition of dilute acid or alkali. Hydrogen sulfide precipitates antimony sulfide slowly from an acidified solution. By altering -the respectiveproportions in.

the example there canbe. obtained, for example,

complex salt possessing a "lowerantimony icon Example 3.A suspension of antimonic acid, freshly produced from 100 grams of antimony pentachloride, is added to a solution of 100 grams of sodium pyrogallol disulfonate in 300 com. of water. When heating the mixture thus prepared on the water bath a clear solution is soon obit is a faintly colored powder which readily dissolves in water.

In an analogous manner complex salts of pentavalent antimony with pyrocatechin disulfonic acid, pyrogallol disulfonic acid, pyrocatechin car-' comprises reacting upon, potassium pyrogallol disulfonate with diethylaminoethanolantimonate in the presence of water. u I

2. The process which comprisesreacting 'iipon potassium pyrogallol disulfonate with diethylaminoethanolantimonate in the presence, of water and neutralizing the solution by the addition of an aqueous.diethylaminoethanolsolutiona pound, of pentavalen't antimony, .with. pyrogallol disulfonic. acid, said product being a faintly.

colored powder, soluble in water anddisplaying a therapeutic action.

4. Intheprocess of preparing complex com ponds of pentavalent antimony, the step which comprises reacting upon potassium pyrocatechin disulfonate with antimonic acid in the presence ofwater. .1

5. In the process ofpreparing complex .componds of pentavalent antimony, the step which comprises reacting upon;sodium pyrogallol disulfonate with antimonic acid in thepres'ence of water. 1

16. The process which comprises reactingupon potassium pyrocatechin- 'disulfonate with antimonic acid in the presence of water and neutralizing the solution by the addition of dilute caustic potash solution.

7. The process which comprises reacting upon sodium pyrogall'ol disulfonate with antimonic acid tralizing the solution by the-addition of dilute caustic soda solution 8. In the process of preparing complex com-- poundsof pentavalent antimony, the stepzwhich comprises reacting upon .a polyhydroxy benzene compoundselected from the group consisting'of pyrogallol and pyrocatechine sulfonic and car.-

.in the presence of vwater and" neu-' ing of antimonic acid and a water-soluble antimonate, in the presence of water, and neutralizing the solution by the addition of an alkali capable of forming a water-soluble product.

10. The neutral complex organosmetallicgcompounds of pentavalent antimony with a"polyhydroxy benzene compound selected from the group consisting of pyrogallol and pyrocatechin, containing at least one acid group capable of forming a water-soluble salt, which acid group: is at- 10 tached to'a basic radical of a water-soluble a1- kali, said products being generally faintly colored powders, soluble in water and displaying a therapeutic action.

11.--The neutral complex organo-metallic com- 15 pound of pentavalent antimony with pyrogallol noethanol, said product being a faintly colored powder, soluble in water and displaying athera- 2 peutic action. 3'. The neutral c'omplex organo -metallic com- 12. The neutral complex'organo -metallic'comi pound of pentavalent antimony I with pyrogallol' dlsulfonic acid, in whichcompound the acid ra'dicals are connected to sodium; said product being afaintly colored powder, soluble in tirater and displaying a therapeutic action. "1 13. The neutral complex organo-metallic'com pound of pentavalent antimonyiwitha'pyro' catechin disulfonic acid, in which compound the 3 acid radicals are connectedto an alkalimetalf said product being a whitish powderj solulo'le'in' water and displaying atherapeutic action. 14. The neutral complex 'or'gano metal'lic com.

pound of pentavalent' antimony with pyrocate- 35 chin disulfonic acid, in which compound the; acidradicals are connected topotassium, *sai'd prodnot being a whitish powder,so1ub1e in water and displaying a therapeutic action.

15. The neutral complex,organo-metalliccomI *Qa pounds of pentavalent antimony with apolyf hydroxy benzene compound selected from the; group consisting of 'pyrogallol and pyrocatechiri sulfonic acids, in which thesulfonic acid groups are attached toa basic radical"of awater soluble' alkali, said products being'generally faintly col ored powders, soluble in water' and displaying" a'therapeutic action. I V v ft" 16. The neutral complex organo-'metal1ic'jcom-" pounds of pentavalentflantimony with "a' poly hydroxy benzene compoundselected'from the; group consisting of pyrogallol and'pyrocat'echin: carboxylicacids, in which'thej carboxylic acidgroups are attached'to a basicradicalof a wa 1y faintly colored powders, soluble'in water; and

ter-solublealkali, said products beinggeneral- .1 

